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iTunes 8.1 breaks syncing with 2nd gen iPod shuffle

14674 Views 73 Replies Latest reply: Nov 5, 2009 11:40 AM by poeskaleidoscope RSS
  • Jason L Community Hosts Community Hosts (9,250 points)

    Try installing iTunes version 8.1.1.
    You can download it here: or run software update as shown in the articles below.

    If you have a Mac, this article: will walk you through updating the Apple software.
    If you have a PC, this article: will walk you through updating the Apple software.

    MBP 2.4 with 4GB ram, Mac OS X (10.5.6), Original iPhone, iPhone 3G, Apple TV, Airport, iMac, iPod Video, Nano, Hi-Fi..
  • mikeoliver2106 Calculating status...
    thanks for your response, but unfortunately 8.1.1 doesn't correct the problems either. do you know of any other potential solutions? thanks
    Windows XP
  • Logainne Calculating status...
    Currently Being Moderated
    Apr 6, 2009 4:31 PM (in response to KepiSW)
    Thanks SO MUCH for posting this. I have a 2nd gen iPod shuffle and a MacBook Pro and thought I was losing my mind. I guess I am still losing my mind, but at least now I know it's on account of Apple. Ugh.
    iMac 4,1, Mac OS X (10.4.7), CPU Type: Intel Core Duo
  • BenjaminL Calculating status...
    Currently Being Moderated
    Apr 6, 2009 6:01 PM (in response to KepiSW)
    This situation is a total disgrace. They might have considered posting a warning: "Caution: if you accept this upgrade, your hardware will break."

    It is a situation worthy of Microsoft, not the Apple of legend.
    Dell XPS, Windows Vista
  • Joe Canadian Calculating status...
    My 2nd Gen Shuffle's syncing behaviour has not changed with the upgraded 8.1.1 iTunes. So sad.....
    24 " iMax, Mac OS X (10.5.6)
  • Thomas Tibbitts Level 1 Level 1 (5 points)
    8.1.1 FTL

    My 2nd Gen. Shuffle still misbehaving (just as it has since iTunes 8.1)
    Mac Mini, Mac OS X (10.5.6), iPod Shuffle 2G
  • Larry Duran Calculating status...
    Try a "restore" next time you sync your Shuffle in iTunes.
    I was also experiencing the problems in 8.1. Found the same in 8.1.1. Then I restored the Shuffle's firmware and it all seems to be working normally (for me),
    iBook G4, Mac OS X (10.4.11), 2G iPod Shuffle
  • Andrew Heiss Calculating status...
    Restoring the firmware didn't fix it here... none of the metadata ever gets synced right anymore and the play order is still messed up. I tried created a mirror playlist, hoping that would help, but that didn't do anything either.

    MacBook, Mac OS X (10.5.6), 2nd gen Shuffle
  • David Bales Calculating status...
    Do not install 8.1.1!

    Another new Feature of this "upgrade", is that I can no longer create lists from the Shuffle itself.

    I used to be able to drag a selection of tracks from the unit, to an existing play list, which would allow me to at least manually compare tracks, and manipulate their order.

    I can no longer even do this with the upgrade!

    Also, as has been the case for the last two upgrades, I can no longer play selections on the device playlist itself when it is attached via USB.

    On the plus side: it no longer hangs iTunes periodically like it used to when doing this.

    On the minus side: I cannot reset tracks to the beginning, or monitor the current location in the file, or see the amount of unheard material from within iTunes.

    And since there is no display on the Shuffle, "Houston, we have a problem."

    Still patiently waiting for basic functionality to return.
    *iMac 2.8G Duo/2G/500G *iBook G4 1G/1G/125 *dp800/1.5GB/120G/120G/120G/250G, Mac OS X (10.5.5)
  • David Bales Level 2 Level 2 (280 points)
    OK, did the reset as Larry suggested.

    It reset the Shuffle using the current iTunes version, and I have much improved performance since my last post.

    I can play tracks on the iPods playlist while plugged in with USB.

    Playcounts now update for me.

    I can add songs on the iPod's list to a new iTunes playlist (sometimes).

    It seems to remember much more effectively the playhead position on a track.


    Still allows duplicates without a warning.

    Doesn't seem to allow or remember sorting of iPod track order within iTunes (date, title, or artist).
    *iMac 2.8G Duo/2G/500G *iBook G4 1G/1G/125 *dp800/1.5GB/120G/120G/120G/250G, Mac OS X (10.5.5)
  • Plynke Calculating status...
    Currently Being Moderated
    Apr 7, 2009 9:12 PM (in response to KepiSW)
    I found another fix. After I downgraded back to 7 I could play from my itunes again, but it still wouldn't sync the stopping point when I listen to half a chapter in my audio books. I fixed this! You have to right click on the song and go into "Get Info". Under the options tab there is an option for "Remember Playback Position". It used to do this automatically, but I guess it broke with the upgrade. Hope this helps someone!
    Windows XP
  • Andrew Heiss Level 1 Level 1 (0 points)
    Currently Being Moderated
    Apr 8, 2009 3:23 PM (in response to KepiSW)
    I was fortunately able to roll back to 8.0.2 and recreate my library and everything is back to normal. I'll definitely be avoiding all future updates until they find a fix.
    MacBook, Mac OS X (10.5.6)
  • Riverside_Guy Calculating status...
    I generally always go for an upgrade to Apple software. No longer.

    I don't do podcasts, I have my shuffle to... listen to music. In point of fact, I have only recently noticed issues... but I think MY issues may have started with 8.1.1... but onto the details.

    I have a very specific set-up that I use. I have a smart playlist that lists only files that have 0 as the play count. I fill my 2g shuffle from this list. Each time I sync, the files I have listened to fall of this list. I always "fill randomly" and play in continuous mode. Thus I get shuffled songs that won't get added back in until ALL my songs are played... at which time I reset the play counts back to zero.

    So the list of songs on my shuffle will show (in iTunes) exactly what order they will play in... remember they are randomly added to start with. Thus, when I sync again, I'll see the date of sync and a 1 play count at the top of the list.

    What I have seen recently is that it seems to want to skip files at the top of the list, but WILL tag them as having been played. The last time I did this, I noticed it didn't start with the top listed song, but one under it. Even a triple click brought mew to song #2. After a couple dozen songs, I synced again. Wouldn't you know, my #1 song was listed as being played, however, it did NOT play.

    First, has anyone seen anything like what I am seeing? Like I said, I've noticed it in the past 2-3 weeks, so maybe it's something that started with 8.1.1???
    G5 Dual 2.7G, Mac OS X (10.4.11)
  • user2009 Calculating status...
    Currently Being Moderated
    Apr 10, 2009 4:27 PM (in response to KepiSW)
    Well count me in on this issue as well. Wow, never had to post here before this week. I all but pulled my hair out with my 2nd gen blue last night....i tried all my computers, of which are running the most recent iTunes. To to let people know, i have a 3rd gen and a 1st gen shuffle as well. Im about ready to go back to the 1st gen and return both the 2nd & 3rd gens this weekend!!!!!

    1 issue last week-still happening with the 3rd gen
    1 issue this weekwith the 2nd gen.
    next week??????????????
    PC, Windows Vista, xp & win7 64 machines
  • grizzlehizzle Level 1 Level 1 (0 points)
    Currently Being Moderated
    Apr 12, 2009 12:54 PM (in response to KepiSW)
    iTunes 8.1.1, experiencing all problems with "update," namely podcasts, syncing, play counts, duplicate tracks, track order, etc. Pity.
    mbp 17" 2.16 ghz core duo, Mac OS X (10.5.6), 2nd gen shuffle


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